Herein is proposed a novel, general method for the practical total synthesis of the 11-desoxy anthracycline antitumor agents: aclacinomycin, cinerubin, pyrromycin, musettamycin, marcellomycin, and rhodirubin. Aclacinomycin has exhibited strong antineoplastic properties but more importantly has been shown to be quite non-cardiotoxic even at high doses, so that it may be superior to adriamycin in treating human neoplasia. Cinerubin also possesses tumor-inhibitory activity, especially against certain adriamycin-resistant tumors, e.g., a subline of P-388 leukemia virus. The other compounds have been isolated only recently and, although the initial screening process has indicated some tumor-inhibitory properties, more testing is necessary. Thus our objective is the synthesis of these antineoplastic agents and their analogues which may have higher potential as cancer chemotherapeutic agents than the natural drugs themselves. The proposed synthetic route to these compounds involves a totally regiospecific approach to the construction of the molecular framework. The key step of our pathway is a Diels-Alder reaction between a readily available hydroxy-naphthoquinone (juglone or naphthazarin) and a bicycle 6-methoxy-2-pyrone derivative with additional functionality in the non-aromatic ring. By analogy to our preliminary results, one would expect this method to produce the entire tetracyclic skeleton of these important molecules in essentially one synthetic step. The conversion of the Diels-Alder adducts into the various antitumor agents would then follow known transformations in analogous systems. This concept of using 6-methoxy-2-pyrones in regiospecific Diels-Alder reactions with asymmetric dienophiles is quite general and should be of great practical use in the field of organic synthesis.